ArcaMax

It’s 11 p.m. on Tuesday, and you’re wrapping up a first date. And it was a pretty good one! It ends with a hug goodbye and tentative plans to get together again for dinner early next week (you know, if you ever hear from him again). As you climb into your Lyft and give a final wave to your date, you’re excited that after a string of "mid" ...Read more

Question: “How do you ask if a guy is ready for a relationship if he is ripe off of a five-year relationship?”

This is a question I received recently, and I get some form of the “How do I know if someone else is ready?” question quite frequently.

My response:

“People are notoriously bad at self-assessing their readiness. The only ...Read more

Dear Anna,

Usually Mariah Carey season is my favorite, but this year I’m struggling. Everywhere I look, people are cozying up, planning cute holiday dates and posting about their jolly AF lives. Meanwhile, I’m single, spending my evenings scrolling through dating apps and wondering if I should just settle for someone mediocre so I’m not ...Read more

Dear Anna,

My partner and I broke up in late April but we had a situationship over the summer. I’m a sophomore in college and I’m excited to get back out there. There’s one problem, I have no clue what I’m doing. I’ve only recently started to learn about sexual guilt and shame because I never focused too much on it while in my ...Read more

“How can I write in my online dating profile to attract the type of person I’m looking for?”

This is a question I get, in some form or another, from clients almost daily. In their mind, they have a target partner. Let’s say this “target” is a man in his 60s, well-educated, with grown children, and lives in Philadelphia. Or maybe ...Read more

Dear Anna,

My fiancee and I have been together for three years, and I thought everything was great. Last night, however, during dinner, she brought up something that completely blindsided me: the idea of us each having a "pass" to sleep with someone else before the wedding. She said it would be healthy for our relationship and help us start our...Read more

“Should sex with one person mean you stop going on dates with other people?”

This is a question someone asked me recently. In my line of work as a dating coach, things come up in all areas of the early dating process—how to use the apps efficiently, what to do/say on a first date, when/what to text, how to build connection and chemistry, ...Read more

Dear Readers: Since announcing my departure from writing this syndicated column, I have heard from scores of people across various platforms, thanking me for more than two decades of offering advice and wishing me well in my “retirement.” I am very touched and grateful for this outpouring of support.

The thing is – I don’t think of ...Read more